Kissimmee vacation rentals

We found 213 vacation rentals in Kissimmee — enter your dates to book direct

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Book direct on Houfy and find a vacation rental that matches your expectations among all these great properties in Kissimmee. Each of the accommodations are being offered directly by owners and managers. Book direct and save up to 25% in commissions and service fees on Houfy.

Featured vacation rentals on Houfy

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Ocean Front Villa, Private Pool, BBQ and more!

Ocean Front Villa, Private Pool, BBQ and more!

Ocean Front Villa, Private Pool, BBQ and more!

5 Bedrooms  4 Bathrooms
4.91IconIconIconIconIcon22 reviews
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The Villa Pine

The Villa Pine

Quiet Villa in Enchanting Beach Town 2.5 blocks to Ocean 194 Reviews on Vrbo!

4 Bedrooms  2.5 Bathrooms
4.84IconIconIconIconIcon348 reviews
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Luxurious Canal Front Home in Islamorada

Luxurious Canal Front Home in Islamorada

Unique 4-Bedroom, 3-Bathroom Canal Home with Private Pool and Beach Access in Beautiful Islamorada

4 Bedrooms  3 Bathrooms
4.94IconIconIconIconIcon16 reviews
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Stylish Getaway in the Heart of Wynwood ~ Balcony!

Stylish Getaway in the Heart of Wynwood ~ Balcony!

Stylish Getaway in the Heart of Wynwood ~ Balcony!

2 Bedrooms  2 Bathrooms
5IconIconIconIconIcon4 reviews
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Paradise Found! Beautiful Oceanfront house

Paradise Found! Beautiful Oceanfront house

Beautiful Oceanfront house with dock, Kayaks and Bikes

3 Bedrooms  2 Bathrooms
5IconIconIconIconIcon43 reviews
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Pompano Beach Area Apartment

Pompano Beach Area Apartment

Excellent Location, Golf, Casino, Shopping, Restaurants

2 Bedrooms  2 Bathrooms
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Charming Studio walking distance from The Beach!

Charming Studio walking distance from The Beach!

Lovely Small studio 6 minute walk from the beach. Bring your partner or your kids!

0 Bedroom  1 Bathroom
5IconIconIconIconIcon1 review
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Beach House Villa Salgado With Pool Near 7 Beaches

Beach House Villa Salgado With Pool Near 7 Beaches

Vacation Home, Private Pool, 7 Minutes to Mar Chiquita, Manati Puerto Rico,

9 Bedrooms  5 Bathrooms
4.63IconIconIconIconIcon24 reviews

Last minute specials on Houfy

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Encanto- 2 Bedroom Beachfront Condo - Simpson Bay!

Encanto- 2 Bedroom Beachfront Condo - Simpson Bay!

Encanto- 2 Bedroom Beachfront Condo - Simpson Bay!

2 Bedrooms  2 Bathrooms
5IconIconIconIconIcon21 reviews
$3700.71
$3737.35 | 10% OFF
Dates: Mar 17 2024 - Mar 28 2024
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Encanto- 2 Bedroom Beachfront Condo - Simpson Bay!

Encanto- 2 Bedroom Beachfront Condo - Simpson Bay!

Encanto- 2 Bedroom Beachfront Condo - Simpson Bay!

2 Bedrooms  2 Bathrooms
5IconIconIconIconIcon21 reviews
$1028.46
$1634.10 | 40% OFF
Dates: Dec 11 2023 - Dec 14 2023
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Riley's Retreat + Cottage

Riley's Retreat + Cottage

Private pool, hot tub, game room & gorgeous ocean views

6 Bedrooms  5 Bathrooms
$189270.00
$236418.75 | 20% OFF
Dates: Aug 26 2023 - Dec 31 2023

Most viewed vacation rentals in Kissimmee

Our guests viewed these book direct rentals the most.

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Beautiful cozy Retreat near Disney- spacious condo

Beautiful cozy Retreat near Disney- spacious condo

Condo • Kissimmee
3 Bedrooms • 2 Bathrooms
4.84IconIconIconIconIcon100 reviews
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Charming Home Perfect for Relaxation and Gateaway

Charming Home Perfect for Relaxation and Gateaway

Vacation Home • Kissimmee
4 Bedrooms • 2 Bathrooms
5IconIconIconIconIcon35 reviews
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Enchanted Rose Villa

Enchanted Rose Villa

Vacation Home • Kissimmee
10 Bedrooms • 8 Bathrooms
5IconIconIconIconIcon1 review
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VENETIAN BAY (2280SV)

VENETIAN BAY (2280SV)

Townhome • Kissimmee
3 Bedrooms • 2 Bathrooms
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Brand-new Storey Lake 9-bedroom villa w/ lake view

Brand-new Storey Lake 9-bedroom villa w/ lake view

Vacation Home • Kissimmee
9 Bedrooms • 5 Bathrooms
5IconIconIconIconIcon42 reviews
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Storey Lake townhouse 4 BD/3 BA - Sleeps 10

Storey Lake townhouse 4 BD/3 BA - Sleeps 10

Townhome • Kissimmee
4 Bedrooms • 3 Bathrooms
4.85IconIconIconIconIcon61 reviews
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The Magical Mansion

The Magical Mansion

Villa • Kissimmee
8 Bedrooms • 5 Bathrooms
5IconIconIconIconIcon5 reviews
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Lakeside Villa

Lakeside Villa

Villa • Kissimmee
3 Bedrooms • 2 Bathrooms
4.78IconIconIconIconIcon78 reviews

Search 213 vacation rentals in Kissimmee

Search vacation rentals, beach rentals and condos in Kissimmee, Florida, United States

Recommended vacation rentals in Kissimmee

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Luxury lake view villa near Disney w. private pool

Luxury lake view villa near Disney w. private pool

Vacation Home • Kissimmee
4 Bedrooms • 2 Bathrooms
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LAKE BERKLEY (975PT)  - 4BR 3.5BA Townhome

LAKE BERKLEY (975PT) - 4BR 3.5BA Townhome

Townhome • Kissimmee
4 Bedrooms • 3.5 Bathrooms
5IconIconIconIconIcon3 reviews
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Princess Penthouse- sleeps 8 w/ lazy river

Princess Penthouse- sleeps 8 w/ lazy river

Condo • Kissimmee
2 Bedrooms • 2 Bathrooms
4.89IconIconIconIconIcon19 reviews
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Venetian Bay, 4 Bedroom Townhouse, Sleeps 10

Venetian Bay, 4 Bedroom Townhouse, Sleeps 10

Townhome • Kissimmee
4 Bedrooms • 3.5 Bathrooms
4.93IconIconIconIconIcon95 reviews
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Wonderful property 4 bed, 3 bath at Paradise Palms

Wonderful property 4 bed, 3 bath at Paradise Palms

Vacation Home • Kissimmee
4 Bedrooms • 3 Bathrooms
4.8IconIconIconIconIcon54 reviews
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Bella Vida Dream

Bella Vida Dream

Townhome • Kissimmee
4 Bedrooms • 3 Bathrooms
5IconIconIconIconIcon54 reviews
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Enchanted Hideaway

Enchanted Hideaway

Vacation Home • Kissimmee
6 Bedrooms • 4.5 Bathrooms
5IconIconIconIconIcon1 review
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🌴Spacious 4BD/3BA Min➡️Disney Universal Seaworld

🌴Spacious 4BD/3BA Min➡️Disney Universal Seaworld

Townhome • Kissimmee
4 Bedrooms • 3 Bathrooms
4.78IconIconIconIconIcon9 reviews

Vacation houses with pools in Kissimmee

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LB4703-♥ Elegant ⭐⭐⭐⭐⭐ w/Pool °o° Disney Area No Carpet

LB4703-♥ Elegant ⭐⭐⭐⭐⭐ w/Pool °o° Disney Area No Carpet

Villa • Kissimmee
4 Bedrooms • 2 Bathrooms
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Disney-Universal, South Facing Pool, Game Room

Disney-Universal, South Facing Pool, Game Room

Vacation Home • Kissimmee
3 Bedrooms • 2 Bathrooms
4.96IconIconIconIconIcon25 reviews
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Kawaii Disney Villa

Kawaii Disney Villa

Villa • Kissimmee
5 Bedrooms • 5 Bathrooms
5IconIconIconIconIcon2 reviews
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BV1031- Private Pool Townhouse near to Disney - Bella Vida

BV1031- Private Pool Townhouse near to Disney - Bella Vida

Townhome • Kissimmee
3 Bedrooms • 2.5 Bathrooms